Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

HRID 490691Notes

Reaction equation

HRID 490691 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=O)[CH2:7][O:8][C:4]=2[CH:3]=1.C1(P(=[CH:31][C:32]([O:34][CH3:35])=[O:33])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[CH3:35][O:34][C:32](=[O:33])[CH2:31][C:6]1[C:5]2[CH:10]=[CH:11][C:2]([OH:1])=[CH:3][C:4]=2[O:8][CH:7]=1

Participants

3

Reactant 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 2357176-Hydroxy-3-coumaranone

Product 1

HCID 20770861Methyl 2-(6-hydroxy-1-benzofuran-3-yl)acetate

Procedure

A mixture of 6-hydroxy-(2H)-benzofuran-3-one (5.0 g, 33.3 mmol), methyl (triphenylphosphoranylidene)acetate (25.0 g, 73 mmol), and xylenes (100 mL) is refluxed 6 hr. The reaction is concentrated and diluted with enough 1M aqueous hydrochloric acid to adjust pH to 2-3. The product is extracted into ethyl acetate (3×100 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is purified via silica chromatography eluting with 7:3 hexanes:ethyl acetate to afford the product as a orange oil, 1.3 g, 20%. MS M++1 207. The structure is confirmed by 1H NMR spectroscopy.

Workup

  1. temperatureis refluxed 6 hr
  2. concentrationThe reaction is concentrated
  3. additiondiluted with enough 1M aqueous hydrochloric acid
  4. extractionThe product is extracted into ethyl acetate (3×100 mL)
  5. dry with materialThe combined extracts are dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified via silica chromatography
  9. washeluting with 7:3 hexanes

Sources & evidence

ORD record
ord-340e50af0cd1451885872d5c97e544c0
Source dataset
uspto-grants-2009_05
Patent number
US07528160B2

Reaction notes

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